1. Field of the Invention
The present invention relates to novel oat-lipid based surfactants and derivatives, and emollients, their process of manufacture, their use in the production of surface active derivatives, non-surface active esters, and ester emollients, and skin and hair care preparations containing the surfactants, derivatives, and emollients. The surfactants and fatty ester derivatives are useful as emollients, dispersants, emulsifiers, and conditioners for hair care and skin care products.
2. Description of the Related Art
Surfactants and derivatives are known for a variety of different applications for cosmetic, pharmaceutical, and medicinal purposes.
Numerous references describe the production and use of surface active derivatives or non-surface active esters, and ester emollients. For example, it is known to use oats and oat extract in cosmetic preparations to obtain the benefits of mildness, antioxidant properties, etc. Surfactants and fatty derivatives useful as emollients, dispersants, emulsifiers and conditioners for hair and skin care products are commonly produced from a wide variety of fatty acids, fatty alcohols and amines, polyamines, dialkyl propylamines, alkanolamines, etc. However, none of these references teach or suggest the specific novel oat-based surfactants made from the fatty oil triglyceride obtained from oats, or OFTG, of this invention or the use of OFTG to produce surface active derivatives or non-surface active esters, and ester emollients for cosmetics and personal care products.
More specifically, oat-based compositions are disclosed in U.S. Pat. Nos. 5,620,692 and 5,622,690 to Potter et al. assigned to Nurture, Inc. of Missoula, Mont. The disclosures of these patents are incorporated herein by reference.
U.S. Pat. No. 5,620,692 to Potter et al. discloses a process for preparing oat oil compositions having antioxidant and dermatological properties.
U.S. Pat. No. 5,622,690 to Potter et al. discloses a method for reducing sunburn by applying a topical formulation comprising an amount of a free flowing seed derived material, preferably oats, having a protein content of between about 1% to 50%, and a average particle size from 1.0 um to 600 um, to skin prior to exposure to ultraviolet radiation.
U.S. Pat. No. 4,014,995 to Juliano et al. discloses a liquid cosmetic preparation comprising a colloidally stable dispersion of 1 to 10% by weight of oat flour in a liquid vehicle. The oat flour is obtained by grinding oat flakes and screening for the preferred particulate size. The oat flour functions to moisturize the skin.
U.S. Pat. No. 4,211,695 to Oughton discloses a process for separating comminuted oats into fractions such as bran, oat oil, flour and protein-enriched or protein deficient flours, for use in the food industry. The process comprises admixing comminuted dehulled oats with an organic solvent for oat oil, and subjecting the admixture, in the form of a slurry, to centrifugal force.
U.S. Pat. No. 4,211,801 to oughton discloses a process for separating substantially gum-free flour from oats, comprising admixing comminuted oats with a solvent for oil in the oats and separating substantially gum-free flour from the admixture, and recovering oat oil from the solvent. The products are used in the food industry.
U.S. Pat. No. 5,026,548 to Evans discloses a surfactant for use as a viscosity reducing agent in chocolate, produced by extracting oats with an aliphatic alcohol, extracting the alcohol extract with methanol, and evaporating the methanol.
U.S. Pat. No. 5,552,135 to Cioca et al. discloses a sunscreen composition comprising an oat extract, a sunscreening agent, and a vehicle for enabling said composition to be applied to the skin.
U.S. Pat. No. 5,888,515 to Albert et al. discloses a topical composition for treating poison ivy comprising jewelweed extract, plantain leaf extract and a quantity of an aqueous colloidal dispersion of oat grains, in admixture. The colloidal oat dispersion acts as an excipient and delivery agent for the jewelweed and plantain enzymes and provides anti-inflammatory and anti-itch effect.
U.S. Pat. No. 5,589,195 to Potter discloses a method of forming a film on a surface comprising providing a film-forming emulsion comprising an emulsifier consisting essentially of a proteinaceous particulate matter derived from oat seed.
U.S. Pat. No. 5,817,608 to Bell discloses a cleansing composition having a silicone conditioning agent, and refined oats that have been at least partially defatted and from which at least some of the bran has been removed, so that the conditioning agent is carried by the refined oats.
U.S. Pat. No. 5,863,945 to Murayama et al. discloses amide derivatives and skin and hair preparations containing the amide derivatives.
U.S. Pat. No. 5,888,521 to Zimmerman discloses a composition comprising a hydroxycarboxylic acid (such as glycolic, lactic, citric or malic acids) and oat extract, where the oat extract contains less than about 1% beta-glucan. The composition is applied to the skin to increase the rate of skin exfoliation.
However, among the foregoing patents, none disclose or suggest the specific novel oat lipid based surfactants and derivatives of the invention, a process of preparing same, or the use of such derivatives and surfactants having mildness and emolliency for cosmetics and personal care products.
It is an object of the invention is to provide novel oat-based surfactants and derivatives which are made from a naturally renewable source.
It is another object of the present invention to provide surfactants and derivatives which are made from oat fatty triglyceride.
It is another object of the invention to provide novel oat-based surfactants and derivatives for use in hair care, skin care and other personal care products.
It is yet another object of the invention to provide novel oat-based surfactants and derivatives which have a usefulness similar to conventional amides and betaines.
A further object of the invention is to provide novel oat-based surfactants and derivatives for use in skin care products where the skin feel is even better than conventional derivatives.
It is a further object of the invention to provide novel oat-based surfactants and derivatives having mildness and emolliency for use in skin care and hair care products.
Yet a further object of the invention is to provide novel oat-based surfactants and derivatives which inherently possess natural antioxidants and vitamin factors for use in skin care and hair care products.
Yet another object of the invention is to provide novel oat-based surfactants and derivatives having very low to negligible toxicological effects.
Another object of the invention is to provide formulations containing novel oat-based surfactants and derivatives which are very mild and have a very low toxicological profile.
Another object of the invention is to provide low-irritation oat-based surfactants and derivatives for skin care and hair care products.
A still further object of the invention is to provide novel oat-based surfactants and derivatives having a fatty acid composition profile close to that of the principal constituents of human skin surface lipids that play a key role in maintaining the normal barrier function of healthy skin.
Another object of the invention is to provide a method of producing mild, emollient hair care or skin care products using oat-based surfactants and derivatives.
These and other objects are accomplished by providing oat-based surfactants and derivatives which are improved as compared to commercially available surfactants and derivatives, as they are made from a naturally renewable source, namely, oats. The surfactants and derivatives are mild and have antioxidancy activity. Skin and hair care formulations containing the surfactants and derivatives of the invention are mild and emollient, have very low toxicological profiles, and are not irritating to the skin.
Major fatty raw materials are fatty triglycerides from sources which are naturally renewable such as coconut oil, soybean oil, castor oil, sunflower oil, corn oil, canola oil, etc. A preferred source is oat seeds.
The surfactants and derivatives and emollients of the invention are made from the fatty oil triglyceride obtained from oats. Such fatty oil triglyceride is called xe2x80x9coat extractxe2x80x9d because it is the raw material obtained by extraction of oat seeds of Avena Sativa with organic solvents.
Oat seeds may be refined, unrefined, or minimally refined, as disclosed in U.S. Pat. Nos. 5,622,690 and 5,620,692 to Potter et al., incorporated herein by reference, to free the proteinaceous matter from the lipids. The lipid portion is called xe2x80x9coat extractxe2x80x9d, xe2x80x9coat fatty oilxe2x80x9d or xe2x80x9coat fatty triglyceridexe2x80x9d, abbreviated herein as xe2x80x9cOFTGxe2x80x9d, commercially available from Nurture, Inc., of Missoula, Mont. as Microat(copyright) afa Complex.
Oat Fatty Triglyceride (OFTG) is essentially made up of saturated and unsaturated fatty acids along with some free fatty acids. It is well known that OFTG contains a high level of natural potent antioxidants, such as an ester of ferulic acid. This compound is structurally similar to the synthetic antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). Additionally, OFTG from oat extract contains tocols including tocopherols and tocotrienols. Furthermore, OFTG contains the three forms of Vitamin E (alpha-, gamma- and delta-tocopherols). It is also known that OFTG contains phenols and phospholipids which behave as antioxidants. Antioxidants scavenge and neutralize free radicals created by normal metabolism or damage to skin cells which may result from exposure to ultraviolet radiation, inflammation, dry skin, psoriasis, dermatitis, burns, and aging. This is useful to prevent and/or treat skin inflammation, aging, and other skin and hair damage mediated by free radicals.
The composition of fatty moieties in OFTG is as follows: Linoleic Acid comprises 38%-42%; Oleic Acid comprises 38%-42%; and Palmitic Acid comprises 14%-17% of the total fatty acid content. Free fatty acids are typically present at 8%. The fatty acid composition profile is of importance because it is close to that of the principal constituents of human skin surface lipids that play a key role in maintaining the normal barrier function of healthy skin.
Surfactants and fatty derivatives useful as emollients, dispersants, emulsifiers, and conditioners for hair and skin care products are commonly produced from a wide variety of fatty acids, fatty alcohols and amines, polyamines, dialkyl propylamines, alkanolamines, etc. Unless otherwise specified herein, the term xe2x80x9cderivativesxe2x80x9d is a broad term meant to include surfactants, nonsurface active esters, and ester emollients.
The following list of reactants and their respective derivatives such as esters, amides, betaines, quaternaries, etc., is exemplary of the type of reactants and derivatives on which the emollient surfactants and derivatives may be based, and, as such, is not to be considered limiting.
Group A (Reactants): Fatty acids or methyl esters of fatty acids or fatty oils sourced from naturally renewable fatty triglycerides of oats. A preferred source is oat seeds for oat-based triglycerides.
Group B (Reactants) may be selected from the group consisting of: Alkanolamines such as Monoethanolamine, Diethanolamine; Dialkylaminopropylamines such as Dimethyl Aminopropyl Amine; Polyamines such as Diethylene Triamine, Triethylene Tetramine; Primary and Secondary amines; and Fatty Alcohols (linear and/or branched) (C8-C22 alcohols).
The preferred reactants used in preparing the surfactants and derivatives of the invention are selected from the group consisting of:
A. OFTG and Monoethanolamine which are reacted to form a product whose proposed INCI name is oat-amide-MEA, tradename NATRLFINE(copyright) A, Finetex, Inc., Elmwood Park, N.J.
B. OFTG and Diethanolamine.
C. OFTG and Monoisopropanolamine.
D. OFTG and Diisopropanolamine.
E. OFTG and Dimethylaminopropylamine which are reacted to form a product whose proposed INCI name is oatamidopropyldimethylamine, whose tradename is NATRLFINE(copyright) MD, Finetex, Inc., Elmwood Park, N.J.
F. OFTG and IsoStearyl Alcohol.
G. OFTG Methylated and IsoStearyl Alcohol which are reacted to form a product whose proposed INCI name is IsoStearyl Oat Fatty Ester, tradename NATRLFINE(copyright) E-18, Finetex, Inc., Elmwood Park, N.J.
H. Reaction Product of (e) above (i.e., NATRLFINE(copyright) MD) and Sodium Monochloroacetate, which are reacted to form a product whose proposed INCI name is oatamidopropylbetaine, tradename NATRLFINE(copyright) AB-40, Finetex, Inc., Elmwood Park, N.J.
I. Reaction product of oatamidopropyl dimethyl amine and diethylsulfate, which are reacted to form a product whose proposed INCI name is Oat-amidopropylDiemthyl Ethyl Ethosulfate, tradename NATRLFINE(copyright) Q, Finetex, Inc., Elmwood Park, N.J.
J. Reaction product of Oat Amide-MEA-Maleate and Sodium Sulfite, which are reacted to form a product whose proposed INCI name is Disodium Oat-Amide-MEA-Sulfosuccinate, tradename NATRLFINE(copyright) SS, Finetex, Inc., Elmwood Park, N.J.
The most preferred reactants are A, E, G, H, I and J.
Reactants A and B are used in either exact stoichiometric proportions, or Reactant A (that is, OFTG) is used in some excess over Reactant B, so that there is no or negligible amounts of free Reactant B as residual in the finished product of the invention.
The novel oat lipid based surfactants and derivatives produced by the process of the invention include:
Group C: The Derivatives of Groups A and B Reactants include the following:
Monoethanolamides, Diethanolamides, Polyamides, Tertiary Acyl Amido Amines, e.g., Acyl Amidopropyl Dimethyl Amines, Amidopropyl Betaines, Amidopropyl Quaternaries, Esters with fatty alcohols (linear and/or branched) and Sulfosuccinamates.
OFTG is used in different ways to produce many of the aforementioned surface active derivatives, or non-surface active esters, and ester emollients. Among the surface active derivatives are:
Monoethanolamides, Monoisopropanolamides
Diethanolamides, Diisopropanolamides
Acyl (Oat Fatty based) Amidopropyl Dimethyl Amines
Betaines
Quaternary Ammonium Compounds
Sulfosuccinamates
Polyamides from Polyamines
Among the non-surface active esters, and ester emollients produced by process of invention are:
Esters with Fatty Alcohols
For example, derivatives such as amides of OFTG/Monoethanolamine; Acyl Amidopropyl Dimethyl Amines of OFTG as Cationic Surfactants; Betaines based on OFTG; Esters of QFTG based Fatty Acids and Isostearyl Alcohol; Quaternaries based on OFTG based Amido-propyl Dimethyl Amine; Sulfosuccinamates based on OFTGxe2x80x94MEA Amides; and Sulfosuccinamates based on OFTGxe2x80x94Iso Propanolamines have been prepared. Derivatives may also include those involving other reactive groups known to those skilled in the art.
In a specific embodiment, and by way of illustration, this invention contemplates the production of the following surfactants and derivatives:
1. NATRLFINE(copyright) A (proposed INCI name: oat-amide-MEA) is the reaction product of OFTG and Monoethanolamine. It is also called OatFattyAmide of Monoethanolamine. It has the following structure: 
where R=oat fatty acids group.
2. NATRLFINE(copyright) T-1 (proposed INCI name: QAT-AMIDE-MEA and Sodium Cocoyl Methyl Taurate) is a blend or mixture of NATRLFINE(copyright) A and Sodium Cocoyl Methyl Taurate.
The structure of Sodium Cocoyl Methyl Taurate is: 
where R=Cocoyl group.
3. NATRLFINE(copyright) MD (whose proposed INCI name is oatamidopropyldimethylamine) is the reaction product of OFTG and Dimethylaminopropylamine. It has the following structure: 
where R=Oat Fatty Acids group.
4. NATRLFINE(copyright) E-18 (proposed INCI name: IsoStearyl Oat Fatty Ester) is the reaction product of OFTG Methylated and IsoStearyl Alcohol. It has the following structure: 
where
R1=Oat Fatty Acids group; and
R2=IsoStearyl Group.
5. NATRLFINE(copyright) AB-40 (proposed INCI name: oatamidopropylbetaine) is a betaine of oatamidopropyldimethylamine ester having the following structure: 
where R=Oat Fatty Acids group.
6. NATRLFINE(copyright) SS (proposed INCI name: Disodium Oat-Amide-MEA-Sulfosuccinate) is the reaction product of Oat Amide-MEA-Maleate and Sodium Sulfite. It has the following structure: 
where R=Oat Fatty Acids group.
7. NATRLFINE(copyright) Q (proposed INCI name: Oat-AmidopropylDimethyl Ethyl Ethosulfate) is a reaction product of oatamidopropyl dimethyl amine and diethylsulfate having the following structure: 
where R=Oat Fatty Acids group.
The derivatives have shown usefulness similar to conventional amides and betaines with the additional benefits of being mild to the skin. Also, skin feel is even better than using conventional derivatives.
Some of these surfactants and derivatives are used in skin care and hair care formulations and dermatological preparations. Personal care formulations prepared according to the invention, which contain the surfactants and derivatives added thereto, can be formed, without limitation, into applications such as solutions, emulsions, gels, solids, emulsions, aerosols, powders, creams, granules, or tablets.
Mildness and emolliency of these derivatives is of importance to the improved skin and hair care products including the surfactants and derivatives of the invention. The inherent presence of natural antioxidants and vitamin factors is the distinct difference in the use of OFTG as opposed to other commonly used fatty triglycerides. One other major aspect of derivatives of this invention is their very, very low to negligible toxicological effects indicating their mildness to skin care products.
Thus, the advantages of the derivatives of the invention include:
Made from naturally renewable source
Mildness of the derivatives
Possible antioxidancy activity
Mildness of the formulations containing the derivatives
Very low toxicological profile
Low irritation
Thus, the novel oat-based surfactants and derivatives of this invention have unique properties in that they are mild to the skin, have very low to negligible toxicological effects, and natural antioxidants and vitamin factors are inherently present. These properties make these derivatives useful as a vehicle or carrier, dispersants, emulsifiers, emollient, solubilizer and conditioners for skin care and hair care formulations such as hair creams, hand cleaners, bath oils, suntan oils, anti-perspirants, perfumes, colognes, cold creams, electric pre-shaves, eye and throat oils, finger nail polish, topical pharmaceutical ointments, lipsticks, stick rouge, skin lotions and creams, skin moisturizers, cleansing creams, and after-bath splash and lotions, as well as other formulations. The foregoing list is only exemplary of the type of compositions in which the oat-based surfactants and derivatives of this invention may be used, and, as such, is not to be considered limiting.
The amount of such oat-based surfactants and derivatives to be used in such compositions is dependent on the type of hair care and skin care compositions, the desired dosage or amount of active ingredient to be delivered, the type and quantity of other ingredients, such as cosmetic ingredients used, the amount and type of functional additives that are utilized, the user""s skin and hair type, and the severity and extent of the skin or hair condition, and other parameters that will be apparent to those skilled in the art. Generally, compositions containing the oat-based surfactants and derivatives of the invention are topically applied in effective amounts to the affected areas of the skin or to hair. Typically, the amount of surfactants and derivatives used ranges from about 1.0% to about 30.0%, by weight, of the skin care compositions. For example, a facial cream may only have about 5.0%, while a massage oil may have up to about 20% by weight. Still higher amounts may be used in, for example, bath oils, e.g. 50%.
Further, the oat-based surfactants and derivatives of this invention possess other unusual physio-chemical properties, which can make them suitable for use as emollient carriers in cosmetic formulations, and for use as solvents and emollient carriers in general cleaning compositions, such as in hand, face, and body creams and lotions. Thus, the oat-based surfactants and derivatives described herein may serve not only as emollients and carriers, but may also exhibit one or more other functions.
The surfactants and derivatives of the invention have properties such as, being less greasy, less oily, low toxicity, ease of emulsification, acid and alkaline stability, the ability to form gels with suspending agents, water solubility/dispersibility, and the ability to act as solvents for many common skin and hair care ingredients.
The following are non-limiting examples of processes for preparing the surfactant and derivative compositions of the invention (Examples 1 to 11), toxicology results for several of said compositions (Example 12), as well as uses of the compositions in specific cosmetic or personal care product formulations (Examples 13 to 19). In the Examples, as well as throughout this application, the chemical and scientific symbols have their customary meanings and all percents are weight percents unless otherwise specified.
Example Nos. 1 through 11 identify surfactants and derivatives produced by the process of the invention. For ease of identification, each ester is identified by both an Example Number and a Reference No., where applicable. This identification system is used in the subsequent Tables Nos. I through VII, as set forth in Examples 13 through 19.